The First Times Always the Hardest
by LittleTayy
Summary: OUaB AU. It's Ruby's first time as one of Madam Cora's prostitutes.


**The First Time's Always the Hardest**

* * *

Cora Mills frowned as she listened to the man on the other end of a phone. His request was…unusual but not the most outrageous thing that had ever been asked. As she listened she couldn't help but smirk as he asked, preferably for a brunette. She had the perfect girl in mind; this would be her second test, to prove she could handle a customer with certain proclivities.

"Sir, I assure you, your request can be accommodated and a girl to your preference will be here waiting. Now, when would you like to schedule your _appointment_ for?" Cora asked as she neatly wrote RR in the timeslot.

Now it was time to find Ruby, her newest girl and tell her that she'd gotten her first appointment. She swept out of the foyer and moved quickly up the stairs, checking the girls' bedrooms first. She opened Ruby's door, expecting to find the young brunette lounging on her bed but instead found the room empty. She was surprised to say the least, the girls usually stayed in their rooms unless they had a customer and Cora was curious as to where her little brunette had wandered off too.

She opened the door of the bedroom next to Ruby's and not surprisingly found Mary Margaret and Belle lounging on a bed together talking. She clears her throat and asks if either of them have seen the new girl. They both stammer for a moment before Belle informs her that Ruby had gone down to the kitchen. Cora smiles and then closes the door again, making her way down to the kitchen in search of her pretty brunette.

"Ruby dear," Cora crows as she finds the young brunette, sitting in the kitchen drinking what looked to be hot chocolate.

Ruby turns to look at Cora, eyes wide, expecting something. Cora does her best not to chuckle as she sweeps further into the kitchen and closer to her new girl.

"Yes Mistress?" Ruby asks, her tongue stumbling over the word, not used to calling someone Mistress so casually.

"You've got your first client today," Cora says as she rakes her eyes over Ruby. The elder brunette was attempting to imagine Ruby in a sexy pirate's costume, and the image she was getting was quite enticing.

"Oh, um...I do?" Ruby replied startled. She had known what she was getting in to as soon as she walked in to the place. She had been here for less than 24 hours though and hadn't yet psyched herself up into what she'd have to be doing. Either way though, she was going to do it because Cora had made her one f her girls and she did not want to disappoint the woman.

"Yes dear, you do. Now, a few things you should be are aware of, we never call the clients by their names. Most want to keep their identities secret and we respect that privacy. Some clients also like to role-play, as is such the case with your client," Cora told her simply. She wasn't going to beat around, not when it came to this.

"Role-play? So he wants me to dress up or something," Ruby asked, her brow wrinkling in confusion as she stared up at Cora.

"That's correct. This is a bit of an unusual request but, he'd like you to dress up as a...pirate," Cora continued dubiously. She had never had a request for one of her girls to be dressed as a pirate and she was curious to see the man behind the request.

"A pirate?" Ruby laughed, not believing her ears. "Who wants to fuck a pirate?"

"That is a rather good question but we accommodate too many fantasies and fetishes here. We do not ask questions and we do not judge. Is that clear?" Cora replied sternly, giving the younger woman an icy stare to show she was serious.

"Yeah, of course," Ruby said quickly, not wanting to get on Cora's bad side just yet.

"Good. Now get yourself presentable, your first client will be here soon."

Ruby nodded her head, standing up as she went to place her mug in the sink. She turned around halfway there however with a question. Thankfully Cora was still by the table and didn't seem to be moving.

"Um...where am I going to get a pirate costume from?" She asked, wondering just how she'd dress up as a pirate.

"We have an extensive collection of costumes. I'm sure you'll be able to find something of the like in there. Ask Regina to show you where it is," Cora explained before she left the room with Ruby staring after her.

Not even an hour later and Ruby was standing in a room, in black booty shorts, long leather boots and a tight midriff peasant top and a red and white bandanna wrapped around her head. Her hair was out and long and she had a small, fake plastic sword tied to her waist. She felt quite ridiculous standing in a room dressed like this but this was what she had to do to survive now and it was far better than living on the streets.

The red hair streaked girl was startled from her thoughts as a somewhat hesitant knock sounded on the door. She wasn't sure what to do but before she could think to do anything a voice outside the door murmured something and then the door opened. She smiled seductively, places her hands on her hips as she looked at the two men just outside the door.

One she already knew was Graham, he worked here too and the other was someone she'd never seen before. Graham gave a quick nod to her before disappearing again, as the other man walked into the room, shutting the door behind him. Ruby could see the man before her looked a little uncomfortable and that made her all the more nervous, not knowing where to start.

"So…" she started awkwardly, taking in the quiet man. He was fairly tall, thick, dark, unruly hair and lean. He wore a long overcoat, his right hand shoved into a pocket and his left fiddling with what looked like a pocket watch. As she spoke the mysterious man looked up at her, his gaze boring into hers much like Cora's had previously.

"What would you like me to call you?" she asked quickly, averting her eyes from his, playing absent-mindedly with the sword at her hip.

"Just call me Captain," the man responded in a British accent that surprised Ruby.

"Well, aye aye then Captain," she whispered huskily, winking at him as she gathered her confidence.

The man grinned devilishly at her and Ruby began to think that this might not be too bad after all.

* * *

_AN: Another Brothel fic. Haha. I really like the idea of Ruby and Cora. _

_Anyway, please review. :) LT._


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